If you arent a pussy, consider Honduras (try to visit La Ceiba, a Caribbean port city in northern Honduras)
There are a healthy amount of US webmasters/adult oldtimers living there already.
If you make local friends in high places, it can be paradise - if you dont, then you will pay Tourist prizes forever
I was considering the place for a long time, but I am not the social type, and would end up getting murdered in 3 weeks or less.